Falling Through New England: Chasing the changing leaves in one of the world’s most beautiful regions

Last Fall, I was lucky enough to travel through the northeast of the United States  – an area known as New England – with my Mum. It was a trip we’d planned to do for many years. Originally, in the Spring, as the leaves on the streets were freshly growing and the flowers freshly blooming; seeing the cherry blossoms in Toronto and Central Park – a sensation that just passed us by for another year.

But over the pandemic, the attention turned to the other side of the tree’s life cycle – the changing of its colours, creating a panoramic of colour in the forests of the region before they fall to the ground, leaving room on the bare branches for the snowfall yet to come. This is a gradual process through October and into November, that differs year to year – and proves even more unpredictable as the years go on.

This is a time of the year well followed by the “leafer” community – people who time their travels out of the city, particularly around this region, to capture the changing colours of New England’s incredible foliage. So, timing our own travels just before Halloween, we embarked to witness all the majesty of the changing leaves across Vermont, Massachusetts, Connecticut and New Hampshire. But it would be above the border in Canada that we started our travels, which I hope sparks some ideas for your own.

Starting the journey in Canada

While you may be better placed to start the journey within New England’s borders, as I’m based in Toronto, it made more sense to start here. But wherever you start – it should be as North in the region as you’re willing to go – as you’ll chase the changing colours as you head south.

We started our journey a week before Halloween in Toronto, Canada, where the leaves were changing colours, but had not yet started to fall, with beautiful views in places like High Park. From there, we took the Via Rail to Montreal – one of my favourite trips in the world.

At just under 5 hours, the journey takes you through some beautiful terrain, and is a smooth and comfortable way to get between two of Canada’s most populous (and popular) cities.

Upgrading to Business Class is a worthy investment and – if you do it early enough – surprisingly inexpensive. You’ll enjoy a Montreal bagel with jam or cream cheese, tea, coffee and juices, shortly after you board in Toronto. A hot lunch is served a bit after Kingston, which serves as the halfway point on the journey. Wines, beers and spirits come complimentary, with incredibly kind, helpful staff, refilling water bottles and giving you what you need.

The trees were similarly colourful as we arrived in Montreal – with bright reds and yellows aligned on the waterfront and the sun still beaming down creating a warm and inviting atmosphere. We would spend a night here before making our way south into New England – just a short bus ride into Vermont where our New England journey would start.

Burlington, Vermont

Just two hours from Montreal, Burlington, Vermont served as a perfect place to start the New England adventure. It was my second visit to the city, which serves up some of the region’s best cuisine and nature.

We stayed at the stunning Hotel Vermont, a boutique, luxury, sustainable hotel that opened in 2013 and was less than five minutes walk from the bus depot. We would rent a car here later on to continue our journey, but for now we remained on foot, exploring the beautiful Waterfront Park on Lake Champlain, which separates Vermont from New York State, sitting to the west.

The leaves here were bright and yellow, and starting to fall over the trails that lined the park against the water. The trees in the downtown promenade (the Church Street Marketplace, pictured above) were much the same, decorating the brick laden pedestrian only area with a vibrant colour. Here, you’ll find fantastic local, independent shopping and dining options throughout.

Of course, enjoying the local cuisine here is a must. Hotel Vermont’s own Juniper Bar and Restaurant was a find, with a beautiful cornmeal trout dish – their take on “fish and chips” – and mouth watering carrots and a small salad on the side. You’ll see that pictured above alongside photos of the hotel. The peach cider sorbet was a spectacular dessert – that tasted like a peach cobbler in sorbet form. If your mouth isn’t watering at the thought, it should be.

As is typical of Vermont – but the whole New England region – the dishes were locally sourced, and we were delighted to find a local jazz performance in the foyer after the meal.

The nearby Henry’s Diner (which is closed on Thursdays) served up fantastic breakfast and lunches, as did Friendly Toast, just around the corner from the hotel. And if you’re in the mood for some sandwiches and baked goods, the August First Bakery Café is open until 3pm, with the maple biscuit worth the price of admission alone. I had an absolutely delicious sandwich here, with incredible focaccia bread.

Having taken in the beautiful food and surrounds of Burlington, we rented a car and started to head towards Lincoln, New Hampshire – a two hour drive. On the way, there are plenty of attractions to experience, though the original Ben & Jerry’s Factory is certainly one of the most popular.

I recommend a run through the Flavour Graveyard – where all the flavours of the past are given a morbid finale – before taking a tour of the facility, and trying some of the ice creams on offer. There’s also plenty of great merchandise that you won’t find anywhere else.

The graveyard set the tone for Halloween, which was just around the corner. If you want to embrace this further, be sure to head to the nearby Gold Brook Covered Bridge, also known as “Emily’s Bridge”, which is said to be haunted, and featured some pumpkins at its entryway.

From there, as we made our way to New Hampshire, we passed through the picturesque town of Stowe, a few minutes from the bridge, and 40 minutes from Burlington. It was like something out of a postcard; a town that a show like the Gilmore Girls could have easily been set in.

The town warranted a good wander around, with lovely small stores, and beautiful countryside – still very green in this part of the country. From there, it was 146 km (91 miles, and about 1 hour and 45 minutes) to our first stop in the state of New Hampshire.

Welcome to Lincoln, New Hampshire

Known as the “Gateway to the White Mountains”, Lincoln sits at a higher elevation than everywhere we’d been before, and so a lot of the surrounds had already seen their leaves fall. So while we may have been well placed to come here earlier, it remained a beautiful destination. And many locals said the same time the year prior saw plenty of leaves still out and vibrant – so it’s going to be slightly different each year.

We stayed at the River Walk Resort at Loon Lake, with countless outdoor activities; from a ice skating rink that gets sets up in the winter, an outdoor pool with hot tub, and an indoor hot tub – all under the shadow of Loon Mountain. You can play bocce and there’s a games room, as well as a giant gym in the basement. And, as the name suggests, you’re situated around a beautiful river walk.

It’s a region that demands exploration of its surrounds, be it on foot on the river walk, or on rail – with the nearby Hobo Railway and the Café Lafayette Dinner Train serving scenic experiences where the train itself – and its views – are the destination. I wrote more about the Café Lafayette experience HERE, in which we enjoyed a delicious five-course meal over a slow moving, two hour, twenty mile journey, with dome seating for the best views, and light jazz playing in the background.

And of course there’s plenty of driving to be done – a 46km drive up to the incredible Omni Mount Washington in the White Mountains didn’t bring the colour we were hoping for, but was a stunning journey – and one I would do earlier in the season next time.

It also screams haunted hotel in the mountains… and I am absolutely here for that vibe.

Lee, MA and the Berkshires

From there, we headed further south to Lee, Massachusetts, which took us to a lower elevation and back towards some of the more colourful foliage we were hoping to experience. On the way, we found more covered bridges – like the White Mountain National Forest Bridge constructed in 1858 and renovated in 1970. This was just outside of North Conway – where you’ll find the Mount Webster Scenic Railroad, amongst some lovely shopping and dining options.

We stopped in Stockbridge on the way to Lee, to experience the Naumkeag Pumpkin Show. The event turns the Gilded Age-style Berkshire public garden and historic home, Naumkeag, into a “celebration of autumn” with more than 1,500 jack-o-lanterns, haunted houses, hot cider and “countless locally grown gourds”. It’s certainly worth experiencing if you’re travelling in October, and tickets for 2024 are already on sale.

We stayed not too far away at the quaint Devonfield Inn, one of the best B&Bs I’ve ever stayed in. Having been occupied by the Halloween experience, we sadly missed the B&B’s “Happy Hour”, from 5pm to 630pm, with wine, cheese and piano on Saturdays. I was promised it becomes quite a singalong. The owners left a note out for us with the keys, and we explored the beautiful accommodation ahead of a restful night.

This older building offered more creature comforts than some five star hotels. Robes were in our sizable room, and drinks were sitting out in the living area for us to enjoy at our convenience. In the morning, we were treated to a lovely breakfast, with a sweet or savoury option available.

It was a short 20 minute walk or 3 minute drive to the main strip of Lee, where we enjoyed dinner – dining at the Salmon Run Fish House, where I was told their Clam Chowder was divine. And they did not disappoint.

The nearby Norman Rockwell Museum is open year round and is one of the best attractions in the area. His studio is open from May to October, and we got one of the final tours before it closed for the season. Stockbridge, where we found the pumpkins earlier, was where he lived at the end of his life, but they moved to studio to the land here, which has a number of walking trails of its own.

This would bring an end to our time in Massachusetts, with Connecticut serving as our next stop.

Off to Connecticut: Mystic and New Haven

After two hours on the road, passing through well known towns like Hartford, we finally made our way back to water level, and the town of Mystic, Connecticut. Yes, this is the town featured in the movie Mystic River, as well as the iconic Mystic Pizza – which is a real dining establishment, still open today at 55 West Main St.

It was here we started seeing leaves that were back at the vibrancy we’d seen a few days earlier back in Vermont, and experienced the ghost tours of the “Jack-O-Lantern Walk” in the Mystic Seaport Museum’s “Seaport Village” – one of my favourite immersive experiences I featured in this article.

Open year round, at the museum you’ll immerse yourself in actual buildings and ships – collected from around New England – from the 1800s. They’re not replications, they’re the real deal, showcasing the bustling maritime trades from the period, while shipsmiths, coopers, woodcarvers and riggers show you how it all worked.

It’s a picturesque, beautiful town that sadly offers limited accommodation, so we weren’t able to stay in the town – rather at a nearby Foxwoods Resort Casino, which was a comfortable room with fantastic views – but without the human touch of our earlier accommodation – especially at the Devonfield Inn. There was some great factory outlet shopping here though – I left with some great Levi’s shirts that I’m wearing as I write this article months later.

We would travel from Mystic River to visit the first planned city in America, New Haven, Connecticut. It’s here you’ll find the iconic campus of Yale University, where. like Rory in Gilmore Girls, we got a tour of the facilities from one of the students. It’s an incredible site, bursting with history. Their library alone is worth the visit, with over 50 million books, including some of the first ever printed. For one, you’ll find the Gutenberg Bible in the Beinecke Rare Book and Manuscript Library.

And as you can see, the colours in New Haven, Connecticut, were incredible.

Our journey would end at the Stony Hill Diner in Bethel, CT, a classic American Diner on the side of Route 6, where we enjoyed a grilled sandwich with tater tots, and made our way across the border to New York (where you can read about our adventures HERE).

Getting my taste of being a “leafer” was one of the best experiences I’ve ever had; and what a treat to get to do it with my Mum, seeing her tick such a notable item off her bucket list.

We experienced both disappointment that we’d arrived after the peak time in the higher elevations, but then such joy when we saw the vibrancy of the areas closer to sea level.

If we’ve done the trip a few weeks earlier, we may have seen even more in some areas – particularly the White Mountains – but then we wouldn’t have seen the way New England celebrates Halloween, which was quite a treat unto itself. And we probably wouldn’t have seen what we did in Vermont and Connecticut.

And the covered bridges are a treat any time of year. Here we are at the White Mountain National Forest Bridge, also known as the Albany Covered Bridge, located in New Hampshire.

So how you time it is up to you, but definitely get over there in October, and be prepared to see a little bit of everything in your journey. And anytime you have a chance to taste the local cuisine, jump on a scenic train ride, or stay at a quaint accommodation option, you’ve got to take it. Beyond the leaves, and the natural beauty, this is what gives this region its character. The people who are devoted to showing off everything that New England has to offer. And it has enough to offer to keep you here for weeks at a time.

Getting to New England

If you want to start at the same place we did, limited flights operate directly into Burlington, Vermont, from cities around the US, and there are more options going through Montreal. You can also fly into New York and travel north – however if you’re chasing the leaves, that is the opposite direction of where you want to travel. You can also look into Boston, and other cities listed in this article, to see who flies in!

This trip was made possible with the support of New England Tourism – Vermont, Massachusetts, Connecticut and New Hampshire – with additional support from Via Rail in CanadaAll photos by the author. This piece was originally published in May 2023, and republished with some minor changes in June 2024. All information was correct as of the later date. 

Larry Heath

Founding Editor and Publisher of the AU review. Currently based in Toronto, Canada. You can follow him on Twitter @larry_heath or on Instagram @larryheath.